{"title":"Superacid-promoted synthesis of imidazole-containing spirocycles","authors":"Jeffrey C. Ferreira, Douglas A. Klumpp","doi":"10.1016/j.tet.2025.134542","DOIUrl":null,"url":null,"abstract":"<div><div>A series of imidazole-containing fluorenyl spirocycles have been prepared from 9-fluorenol derivatives. Highly acidic media and superacid media are shown to promote spirocyclization to this new class of spirocycles. A mechanism is proposed involving fluorenyl cationic species, including dicationic ions. Electrochemical and optical experiments were conducted for the calculation of frontier molecular orbital energy levels. Fluorescence spectroscopy showed that select conjugated fluorophores were intensely emissive in the near-UV visible (blue-purple) spectrum range.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"176 ","pages":"Article 134542"},"PeriodicalIF":2.2000,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402025000985","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/2/20 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A series of imidazole-containing fluorenyl spirocycles have been prepared from 9-fluorenol derivatives. Highly acidic media and superacid media are shown to promote spirocyclization to this new class of spirocycles. A mechanism is proposed involving fluorenyl cationic species, including dicationic ions. Electrochemical and optical experiments were conducted for the calculation of frontier molecular orbital energy levels. Fluorescence spectroscopy showed that select conjugated fluorophores were intensely emissive in the near-UV visible (blue-purple) spectrum range.
期刊介绍：
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
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